This is the task of explorer extension. I know it's possible, yes, but this is a task that goes beyond Callback File System and requires creation of Explorer extension (which is done in user mode). I think that the sites like CodeGuru or CodeProject should have some examples related to this task.

Explorer requests a desktop.ini file for every folder it encounters. You can set an icon for display in that file. You needn't report it's existence to the user (unless the user creates one), but in the event there isn't one you could supply one from a resource that specifies the icon you want to display. Then when Explorer asks for the icon you'll need to supply that too (also from a resource I would guess).

Haven't tried it but I think that will work.

Otherwise you'll need a shell extension (which should be done in c++ no matter what you read about side-by-side execution of .Net Frameworks in v4+)

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